Many (perhaps most) brokerage firms lack provisions for debit cards, certified funds options, wires to third parties, etc.

There are a number great multifamily expert contributors here like @Michael Blank & @Joe Fairless.

@Felix Zaczek V If and when the property goes under contract, a competent real estate attorney would request that as a condition to the sale the property be certified as a 3 unit by the City of Chicago.  

There's nothing wrong with sticking with what works for you & what you're an expert at.There's value to "I'm already an expert at THIS thing that I'm doing" that folks often lose sight of when they get caught up in "you know, in THEORY, bla bla bla."

I've actually been retained as an expert witness to testify against MHC's who have all but threatened their residents and tried to ban outside sales of new and existing homes, require homeowners/tenants to go through their in house sales staff and contractors.

Network with brokers and agents, run your numbers, make offers, perform your due diligence, before you buy call in experts to look at the property, raise more or have enough capital reserved to cover issues that pop up, which they always do, run your numbers, don't overpay for the property and run your numbers.

My name is Gary Pick and I am Certified Residential Appraiser here in Rhode Island. 20 years in Real Estate.

That inspection was to Certify it passes regulations/building code for Owner Occupancy.

Just make sure you hire a PM who is used to dealing with properties in that neighborhood or similar neighborhood unless you are expert in dodging bullets yourself..lol. 

If the P&L is not audited (or at least certified) then I would ask for tax returns and bank statements to verify them.Get financial vacancy numbers vs physical vacancy.